Ms Jamie Grae on crossdressing as an older lady

We asked our 2016 Grand Champion Winner of the 2016 Glamour Girl Picture Contest to share some details of her own journey to female gorgeousness. Ms. Jamie Grae has many fans in our office and we are so happy she has chosen to share a lot more of herself with us all. Let me introduce you to the very lovely Jamie Grae…

“Wow, how do I start this? My name is Jamie Marie Grae and I’m 70 years old.

I identify as a crossdresser. I dress up and go out in public as a girl. You can say, OMG, how does HE do it? Let me tell you, it’s not easy. Really, not easy. For all you “girls” getting out the door for the first time, you know what I’m talking about. FEAR!

Let me tell you the story of “Jamie” getting to where “she” is right now…

First I have to tell you what started this desire to dress up as a girl. I had a beautiful girl in my life, early in my years. That girl was my sister. My sister was GORGEOUS. She was a cheerleader, long haired, slim and had the most gorgeous figure. I always wanted to be as pretty as her one day.

This is where it all started. I was only 13 (I guess) and she was two and a half years older. I would see her tanning in the backyard in her bathing suit, filling it out perfectly with her 36-24-36 figure and I wanted to be her. She was so perfect. I was just a skinny, tall, nerd. I would sneak into her room and “borrow” her bathing suits. I would bring them into the bathroom with socks to stuff the boobs.

It wasn’t until high school that I ever tried to be a girl again.

I was in my senior year of high school and I took a photography class. There were nine girls and I was the only boy. Go figure! Anyway, it was a fun class. I met my first wife in there. The reason for putting this class into my story is that this is the first time I ever applied makeup. Yes, Make up. I had NEVER even thought about putting makeup on until then. Let me tell you how it happened.

One of the assignments for the class was to do portraits of each other. So, we took pics of each other for our “portrait” assignment. I was behind the camera most of the time and the girls, even at that young age, were pretty darn good with makeup. I was amazed at how well they would team up to give each other makeovers. Gosh their pictures looked so good! I was the last one to have my picture taken. I came to school that day in a sport coat, tie, and a white shirt; wanting to look good for my portrait.

However, when I got to class, the girls had a little surprise planned for me. They wanted to apply some makeup to cover my flaws. So, of course, I gave them free range to do whatever they wanted. It was taking a bit long, so I asked them what was going on. They said I was going to be as pretty as them in my portrait. OMG, I was shocked. I resisted, but they were so professional (even at the young age of 16). The last touch was a blonde wig. Then, I knew something was going on. Well, duh. Anyway, when I was done, they showed me in a mirror, what I looked like. I will NEVER, NEVER, forget that moment. I looked so pretty. I had the sheet draped over my shoulders and felt so much like a pretty girl. Here’s the final picture that I submitted for the assignment.

I stared at that pic for weeks. Seeing the woman I could be emerging from this nerdy guy, was mesmerizing to me. Matter of fact, it still mesmerizes me. When I found it for this article, I stared at it for a good 5 minutes.

Now you know how Jamie came to be. Once I got a chance to not just dress, but put on makeup, it was hard to go back.

OK. Now many years in the future, I got married (actually to one of the girls in that class) and had a busy life trying to get ahead. I never dressed or even had the thought of dressing for about 18 years. It all started flooding back to me after my devastating divorce. I lost most of my life in that divorce; the house, my Model A Ford cars, and everything else, except my tools and my Vette. I worked two years paying off that settlement. Bad time for me.

The only positive thing about that time in my life was getting to live by myself. During this time is when I started having the desire to dress as a woman again. Back then, I didn’t have internet and I thought I was the only one on the planet that had this desire. I could buy stockings, skirts, and tops at the local stores but nobody had shoes in a 13w women’s. So, I made my very first pair of heels. They were made of wood with a ½” platform, leather straps, rubber soles, and heels. I wish I had them now. They were actually pretty good looking. Yeah, right!!!! So, I spent my newly single life living in a metal shop building with my two cockers and a bird. That went on for 8 years until my dad and I built houses right next to each other (I was a carpenter). I built my house and did everything including plumbing and wiring, except insulation. As you could probably guess, this put a delay in my crossdressing. Too busy!!! When the house was almost done, I met a girl I was working with at the time and we fell in love. We got married, but before we got married, I told her my dabbling with crossdressing. NOW, I NEED TO TELL YOU. THIS IS THE MOST IMPORTANT THING ABOUT BEING A CROSSDRESSER. BE HONEST. NEVER, NEVER HIDE IT FROM YOUR SPOUSE OR SIGNIFICANT OTHER. TELL THEM EVERYTHING.

So, how many of you have already violated that prime directive? This is number one. You’re doomed if you don’t.

OK, so I told her. It was no big deal. She just paused when I said it and then went on to something else. Well, that’s how I got started dressing for real and getting out. It was 12 years after we got married (me never dressing because once again, beginning a new life and home) that the subject came up. We were watching a movie one night on TV. It was “Tootsie”. I love that movie. Anyway, she brought it up that I mentioned I had dressed up as a woman. She asked if I had done it since we were married. I told her I hadn’t. Well, she said she wanted to see what I looked like.

I think she really thought I would look like a clown.

Now, at this time the internet was a things so, I ordered many things online that would fit my size and one day I showed my wife for the first time, Jamie. I had never done makeup before and I think I looked like a disaster, but I did it and showed her.

Here’s a picture from that night:

I know, I looked horrible, but she liked it. She thought I was gorgeous.

That started a fun bunch of years in my life. She showed me how to walk, pose, and gesture like a woman. She shopped with me and for me. It was great. We had many fun years and went to DLV once. She was getting ill even at that time and didn’t get to go out with me, but a few times. She died of cancer a bit after that and I was alone again.

I’m retired now and living on my own. I enjoy my manly stuff and I enjoy my girlie stuff. My sister knows Jamie and LOVES the fact that she now has the sister she always wanted. I am totally blessed having her for a sister.

Now you know my history. It’s not much different than most other crossdressers. I had my idol; my sister. She was SO GORGEOUS. I had marriages and divorces. I had a wonderful experience with my second wife as she knew about Jamie too.

Now for the present! I haven’t been dressing and going out for very long. I want to kick myself for not getting out earlier. I have a very good friend that found me on the internet that was the one that got me out the door for the first time. I thank her so much for that. I also found a group locally that gets out every Friday night. I still go out with them today. I met my best friends in this group who supported me during the lose of my wife. I love this man (girl) dearly. I am so lucky to have him (her) in my life. When she goes out, she has the knack of drawing girls around us like a magnet. It is so much fun. There’s nothing better than being out with TG’s than being out with GG’s.

OK. I don’t just go out on Friday nights. I go out dressed anytime I want. Even just staying home doing housework, working in the shop, or mowing the grass. Jamie does it all. I even fit in with the “Walmart” crowd. LOL . My bank even knows Jamie. :o)

So you see, I have come a long way. Jamie is half my life. I enjoy being her and I enjoy being James. I’m not transgender. I’m a crossdresser. Just a crossdresser. So what can I tell you about being happy with both sides like I am? I don’t know. We are all so different. BUT, one thing we all have in common is that we all have to get out in public. THAT is the hard part. If you haven’t been out, then this might help you. If you have, but are still nervous about it, I hope this helps you.

Getting out in public dressed as a girl is the scariest thing I have ever done. That first step out the door makes you vulnerable to everyone’s eyes and thoughts. How could I ever do that since I’m a man in a dress? NOT EASY! The whole thing about passing? Don’t believe it or worry about it. I NEVER pass. I am 6’2″ and wear heels which makes me 6’5″ tall. But, you know, people know I’m a guy in a dress, but I look good and I smile almost all the time. You can kill a frown or questionable glance with a smile so fast. I had an older woman at a restaurant once stare at me all during dinner and it was making me nervous. When she got up and left after finishing dinner, she came over to me and told me how beautiful I looked. So, you never know what people are thinking. I’ve learned to take every glance as the other person just wondering what I’m about. My smile back at them says I’m a nice person.

I’ve been very lucky in having the best makeup artist in the country do my make up. I highly recommend Amy of, Just You in Vegas. She made me beautiful for the first time. I actually cried when I saw what I looked like in the mirror. This is Amy and myself after my very first makeover.

I have learned so much over the years from Amy. I have her do my makeup whenever I go to an event and I still learn more each time she does.

This is the result of the last time she did my make up. I still am amazed at how good she can make this 70 year old man look.

To see more gorgeous ladies from recent and past picture contests see our Glamour Boutique contest picture articles section.